Transformation of N,N-diisopropylarylmethylamines into N-isopropylarylmethylamines with molecular iodine

被引：5

作者：

Ezawa, Masatoshi ^{[1
]}

Moriyama, Katsuhiko ^{[1
]}

Togo, Hideo ^{[1
]}

机构：

[1] Chiba Univ, Grad Sch Sci, Inage Ku, Chiba 2638522, Japan

来源：

TETRAHEDRON LETTERS | 2015年 / 56卷 / 48期

关键词：

Molecular iodine; N; N-Diisopropylarylmethylamine; N-Isopropylarylmethylamines; N-deisopropylation; Oxidation; DIRECT OXIDATIVE CONVERSION; ONE-POT CONVERSION; FACILE PREPARATION; AROMATIC BROMIDES; AMINE OXIDATION; TERTIARY-AMINES; ALDEHYDES; CLEAVAGE; ESTERS; SECONDARY;

D O I：

10.1016/j.tetlet.2015.10.044

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N,N-Diisopropylarylmethylamines were smoothly converted into the corresponding N-isopropylaryl-methylamines by the reaction with molecular iodine in the presence of Na2CO3 in chloroform at 60 degrees C. Other related tertiary amines were also transformed into the corresponding secondary amines by the reaction with molecular iodine under the same reaction conditions. (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：6689 / 6692

页数：4

共 38 条

[1]

AUDETTE RJ, 1971, TETRAHEDRON LETT, P279

[2] Preparation of N,N-Dimethyl Aromatic Amides from Aromatic Aldehydes with Dimethylamine and Iodine Reagents [J].

Baba, Haruka ;

Moriyama, Katsuhiko ;

Togo, Hideo .

SYNLETT, 2012, (08) :1175-1180

[3] Benzylic-acetoxylation of alkylbenzenes with PhI(OAc)2 in the presence of catalytic amounts of TsNH2 and I2 [J].

Baba, Haruka ;

Moriyama, Katsuhiko ;

Togo, Hideo .

TETRAHEDRON LETTERS, 2011, 52 (33) :4303-4307

[4]

COOLEY JH, 1989, SYNTHESIS-STUTTGART, P1

[5] AMINE OXIDATION .7. CLEAVAGE OF TETRA-N-SUBSTITUTED 1,2-DIAMINES BY MANGANESE DIOXIDE [J].

CURRAGH, EF ;

HENBEST, HB ;

THOMAS, A .

JOURNAL OF THE CHEMICAL SOCIETY, 1960, (SEP) :3559-3563

[6] Mild Oxidation of Benzylic Amines into Aldehydes Using an Oxidative Polonovski-Like Process [J].

Desjardins, Samuel ;

Jacquemot, Guillaume ;

Canesi, Sylvain .

SYNLETT, 2012, (10) :1497-1500

[7] Transition-Metal-Free Transformation of Aryl Bromides into Aromatic Esters and Amides via Aryl Trichloromethyl Ketones [J].

Dohi, Souya ;

Moriyama, Katsuhiko ;

Togo, Hideo .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (34) :7815-7822

[8] Practical one-pot preparation of ketones from aryl and alkyl bromides with aldehydes and DIH via Grignard reagents [J].

Dohi, Souya ;

Moriyama, Katsuhiko ;

Togo, Hideo .

TETRAHEDRON, 2012, 68 (32) :6557-6564

[9] AMINE OXIDATION .4. REACTIONS OF TERTIARY AMINES WITH N-BROMOSUCCINIMIDE - THE FORMATION OF ALDEHYDES AND SECONDARY AMINES [J].

DUNSTAN, S ;

HENBEST, HB .

JOURNAL OF THE CHEMICAL SOCIETY, 1957, (DEC) :4905-4908

[10] LIGHT-INDUCED, IODINE-CATALYZED AEROBIC OXIDATION OF UNSATURATED TERTIARY-AMINES [J].

GANGLOFF, AR ;

JUDGE, TM ;

HELQUIST, P .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (11) :3679-3682

← 1 2 3 4 →